[5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

Base Information

• Chemical Name: [5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate
• CAS No.: 25030-31-3
• Molecular Formula: C₁₀H₁₄N₆O₆S
• Molecular Weight: 346.324
• Hs Code.: 29339900
• NSC Number: 133114
• DSSTox Substance ID: DTXSID30947893
• ChEMBL ID: CHEMBL18001
• Mol file: 25030-31-3.mol

Synonyms:5'-sulfamoyladenosine

Chemical Property of [5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

Chemical Property:

• Melting Point: 170 °C
• Boiling Point: 762.4±70.0 °C(Predicted)
• PKA: 9.15±0.70(Predicted)
• Flash Point: 414.9oC
• PSA: 197.08000
• Density: 2.24±0.1 g/cm3(Predicted)
• LogP: -0.38990
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 346.06955336
• Heavy Atom Count: 23
• Complexity: 530

Purity/Quality:

97% ^*data from raw suppliers

5’-Sulfamoyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COS(=O)(=O)N)O)O)N
• Uses: 5’Sulfamoyladenosine is used in studies relating to novel parasite inhibitors. In addition, it is used in the design and synthesis of β-ketosulfonamide adenylation inhibitors, as antitubercular antib iotics. 5’-Sulfamoyladenosine is used in studies relating to novel parasite inhibitors. In addition, it is used in the design and synthesis of β-ketosulfonamide adenylation inhibitors, as antitubercular antibiotics.

Technology Process of [5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate

There total 12 articles about [5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

2',3'-O-bis(tert-butyldimethylsilyl)-5'-O-(sulfamoyl)adenosine (863238-53-3) → 5'-Sulfamoyladenosine (25030-31-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield: 50.0%

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (112921-00-3) → 5'-Sulfamoyladenosine (25030-31-3)

Guidance literature:

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate; With water; trifluoroacetic acid; at 20 ℃; for 1h;

With ammonium hydroxide; In methanol; dichloromethane;

DOI:10.1021/ml2000615

Reference yield: 39.0%

6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz)-L-homoserinyl(OBn)sulfamoyl]adenosine (1356085-30-7) → 5'-Sulfamoyladenosine (25030-31-3) + 5'-O-(N-homoserinylsulfamoyl)adenosine

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In water; isopropyl alcohol; at 70 ℃; for 2h; under 37503.8 Torr; Continuous-flow hydrogenation reactor;

DOI:10.1016/j.tet.2011.12.011

upstream raw materials:

2',3'-O-bis(tert-butyldimethylsilyl)-5'-O-(sulfamoyl)adenosine

((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

2',3'-isopropylidene adenosine

adenosine

Refernces

• 1、 Mujumdar, Prashant,Bua, Silvia,Supuran, Claudiu T.,Peat, Thomas S.,Poulsen, Sally-Ann. "Synthesis, structure and bioactivity of primary sulfamate-containing natural products". supporting information. p. 3009 - 3013. Retrieved 2018/04/30.
• 2、 Lukkarila, Julie L.,Da Silva, Sara R.,Ali, Mohsin,Shahani, Vijay M.,Xu, G. Wei,Berman, Judd,Roughton, Andrew,Dhe-Paganon, Sirano,Schimmer, Aaron D.,Gunning, Patrick T.. "Identification of NAE inhibitors exhibiting potent activity in leukemia cells: Exploring the structural determinants of NAE specificity". supporting information; experimental part. p. 577 - 582. Retrieved 2011/10/02.